Acetic Acid → 3-Amino-8-bromo-N,N,-diethyl-5,6-dihydrobenzo[f]quinazolin-1(2H)-one-9-sulfonamide

HRID 381569

Reaction equation

HRID 381569 reaction equation
[NH2:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([S:18](Cl)(=[O:20])=[O:19])[C:15]([Br:17])=[CH:16][C:7]=3[CH2:6][CH2:5][C:4]=2[N:3]=1.[CH2:22]([NH:24][CH2:25][CH3:26])[CH3:23].C(O)(=O)C.CO>O>[NH2:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([S:18]([N:24]([CH2:25][CH3:26])[CH2:22][CH3:23])(=[O:20])=[O:19])[C:15]([Br:17])=[CH:16][C:7]=3[CH2:6][CH2:5][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 8021DiethylamineHCID 1361209353-Amino-8-bromo-5,6-dihydrobenzo[f]quinazolin-1(2h)-one-9-sulfonylchloride

Product 1

HCID 1358381053-Amino-8-bromo-N,N,-diethyl-5,6-dihydrobenzo[f]quinazolin-1(2H)-one-9-sulfonamideYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Amino-8-bromo-5,6-dihydrobenzo[f]quinazolin-1(2H)-one-9-sulfonylchloride (1.10 g, 2.8 mmole) and diethylamine(5 ml) were dissolved in water(15 ml) and heated to reflux for 30 minutes. The reaction mixture was cooled to room temperature and neutralized with dilute acetic acid. The collected precipitate was suspended in boiling methanol, the suspension allowed to cool, and the solid filtered off and dried under high vacuum to give 3-amino-8-bromo-N,N-diethyl-5,6-dihydrobenzo[f]quinazolin-1(2H)-one-9-sulfonamide (0.708 g, 59%). 1H NMR (DMSO-d6, 200 MHz) δ: 1.07 (t, J=7 Hz, 6H, ethyl CH3), 2.54-2.62 (m, 2H, Ar CH2), 2.81-2.88 (m, 2H, Ar CH2), 3.26 (q, J=7 Hz, 4H, ethyl CH2), 6.83 (br s, 2H, NH2) 7.60(s, 1H, Ar), 9.13 (s, 1H, Ar), 10.95 (br s, 1H, NH). Anal Calculated for C16H19BrN4O3S: C,44.97; H,4.48; Br,18.70; N,13.11; S,7.50. Found: C,44.90; H,4.49; Br,18.65; N,13.03; S,7.57.

Workup

  1. temperatureheated
  2. temperatureto reflux for 30 minutes
  3. temperatureto cool
  4. filtrationthe solid filtered off
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-fd832878ef474153835d5463ad9f00f4
Source dataset
uspto-grants-2001_10
Patent number
US06306865B1

Linked notes

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